Water → rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol

HRID 482189

Reaction equation

HRID 482189 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[CH3:35]COCC.O>O1CCOCC1>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:11][CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 36083721-Benzyl-3-tritylglycerol

Product 1

HCID 14584166rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerolYield 78.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

NaNH2 (0.616 g, 15.0 mmol) was added to a flame-dried two-necked 50 ml round bottom flask equipped with a reflux condenser which contained a solution of rac-1-O-benzyl-3-O-tritylglycerol (5.30 g, 12.5 mmol) in anhydrous 1,4 dioxane (30 ml). The reaction mixture was refluxed for one hour under N2. Then CH3I (3.55 g, 25.0 mmol) was added dropwise. The resulting reaction mixture was refluxed overnight. After the mixture had cooled to room temperature, ether and H2O were added. The ether layer was removed and extracted with 1N HCl , H2O, sat. NaHCO3, H2O, and brine. The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give a yellow oil which solidified upon standing. The crude solid was recrystallized with hexanes to yield pure compound 13, rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol (4.32 g, 78.9%).

Workup

  1. customequipped with a reflux condenser which
  2. temperatureThe reaction mixture was refluxed for one hour under N2
  3. customThe resulting reaction mixture
  4. temperaturewas refluxed overnight
  5. customThe ether layer was removed
  6. extractionextracted with 1N HCl , H2O, sat. NaHCO3, H2O, and brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent was removed in vacuo
  9. customto give a yellow oil which
  10. customThe crude solid was recrystallized with hexanes

Sources & evidence

ORD record
ord-f3e3d7352e214416af66cacb4837c803
Source dataset
uspto-grants-1998_08
Patent number
US05795561

Linked notes

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